An understanding of sexual (risk) behavior is necessary to successfully develop prevention and care strategies for the sexually transmitted infections (STI) high-risk group of male sex workers who have sex with men (MSW–MSM). However, limited scientific knowledge is available on sexual (risk) behavior of (home-based) MSW–MSM. This study aimed to gain an understanding of sexual (risk) behavior, factors influencing sexual (risk) behavior, and applied risk-reduction strategies of home-based MSW–MSM. For this qualitative study, semi-structured individual interviews were conducted with 20 home-based MSW–MSM in the Netherlands. The interviews’ recordings were transcribed verbatim and thematically analyzed with Atlas.ti 8. Condom use was reported to be high during anal sex, but low during oral sex and mostly determined by STI risk perception, trust in clients, and sexual pleasure. Many experienced condom failure, while few knew what to do after condom failure and were aware of post-exposure prophylaxis (PEP). Many MSW–MSM had chemsex in the past 6 months in order to loosen up and enhance sexual pleasure. Some were not vaccinated against hepatitis B virus (HBV), mainly due to the lack of information and awareness of HBV vaccination and low risk perception of HBV. The results of this study can be used to tailor future STI/HIV risk-reduction strategies for home-based MSW–MSM and to increase awareness and uptake of available STI/HIV prevention strategies such as P(r)EP and HBV vaccination.